Episode 614 | Deciding When to Quit Your Day Job, Founder Anxiety, and More Listener Questions

In episode 614, Rob Walling chats with fan favorite Derrick Reimer. They start out by talking about Derrick’s decision to take a sabbatical from The Art of Product podcast after co-hosting it with Ben Orenstein for more than 5 years. Then, they answer a handful of listener questions, including when to quit your day job to focus on your startup full-time, coping with anxiety as a second-time founder, and choosing a domain name.

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Topics we cover:

[2:18] Derrick’s decision to take a break from The Art of The Product podcast

[10:22] When should you go full-time on your startup?

[17:20] Before looking for tech firms, should I know the best frontend and backend architecture for my SaaS MVP and then only shop for firms who specialize in that?

[24:13] I'm starting a new SaaS business, and despite a previous successful experience, I can't stop feeling extremely anxious about it. Is this something you're familiar with? How did you deal with it?

[30:34] When choosing a domain name for my startup, should you go with a meaningful and expressive name, but a less serious TLD.io or a somewhat fictional name combined with the best tld.com?

Links from the Show:

• Derrick Reimer @derrickreimer I Twitter
• SavvyCal
• The Art of Product
• Bootstrapped Web
• Summit
• TinySeed
• Bullet Train
• MicroConf Connect
• The Entrepreneur’s Guide to Keeping Your Shit Together: How to Run Your Business Without Letting it Run You
• The Mom Test
• How I Nabbed The .Com for My Bootstrapped Startup Without Spending a Million Bucks
• Lean Domain Search
• The Bootstrapper’s Guide to Outside Funding

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.

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